TY - JOUR
T1 - Diastereoselective synthesis of 6-bromo-6-(1-hydroxyethyl)penicillanate by cross-coupling of 6,6-dibromopenicillanate and acetaldehyde pronmoted with grgnard reagents
T2 - Role of amine ligands
AU - Kuroboshi, Manabu
AU - Mesaki, Keiko
AU - Tateyama, Syoichi
AU - Tanaka, Hideo
PY - 2007/12/1
Y1 - 2007/12/1
N2 - Grignard reagent-promoted coupling reaction of diphenylmethyl 6,6-dibromopenicillanate lb with acetaldehyde in the presence of N,N,N',N",N"-pentamethyldiethylenetriamine took place in a highly diastereoselective manner to give diphenylmethyl (1′R,3S,5R,6S)-6- bromo-6-(l′-hydroxyethyl)penicillanate 2b effectively, which is a potent intermediate for the synthesis of carbapenem antibiotics.
AB - Grignard reagent-promoted coupling reaction of diphenylmethyl 6,6-dibromopenicillanate lb with acetaldehyde in the presence of N,N,N',N",N"-pentamethyldiethylenetriamine took place in a highly diastereoselective manner to give diphenylmethyl (1′R,3S,5R,6S)-6- bromo-6-(l′-hydroxyethyl)penicillanate 2b effectively, which is a potent intermediate for the synthesis of carbapenem antibiotics.
KW - 6,6-Dibromopenicillanate
KW - 6-Bromo-6-(1-hydroxythyl)penicillanate
KW - Amine ligand
KW - Coupling reaction
KW - β-Lactam antibiotic
UR - http://www.scopus.com/inward/record.url?scp=45149084172&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=45149084172&partnerID=8YFLogxK
U2 - 10.3987/COM-07-S(U)47
DO - 10.3987/COM-07-S(U)47
M3 - Article
AN - SCOPUS:45149084172
SN - 0385-5414
VL - 73
SP - 877
EP - 882
JO - Heterocycles
JF - Heterocycles
IS - C
ER -